[3H]N-methyl scopolamine   Click here for help

GtoPdb Ligand ID: 317

Synonyms: [3H]N-methylscopolamine | [3H]NMS
 Ligand is labelled  Ligand is radioactive
Compound class: Synthetic organic
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 59.06
Molecular weight 318.17
XLogP 0.59
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OCC(c1ccccc1)C(=O)OC1CC2C3C(C(C1)[N+]2(C)C)O3
Isomeric SMILES OC[C@H](c1ccccc1)C(=O)OC1C[C@@H]2[C@@H]3[C@H]([C@H](C1)[N+]2(C)C)O3
InChI InChI=1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12?,13-,14-,15+,16-,17+/m1/s1
1. Cembala TM, Sherwin JD, Tidmarsh MD, Appadu BL, Lambert DG. (1998)
Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.
Br J Pharmacol, 125 (5): 1088-94. [PMID:9846649]
2. Cheng K, Khurana S, Chen Y, Kennedy RH, Zimniak P, Raufman JP. (2002)
Lithocholylcholine, a bile acid/acetylcholine hybrid, is a muscarinic receptor antagonist.
J Pharmacol Exp Ther, 303 (1): 29-35. [PMID:12235229]
3. Christopoulos A, Pierce TL, Sorman JL, El-Fakahany EE. (1998)
On the unique binding and activating properties of xanomeline at the M1 muscarinic acetylcholine receptor.
Mol Pharmacol, 53 (6): 1120-30. [PMID:9614217]
4. Christopoulos A, Wilson K. (2001)
Interaction of anandamide with the M(1) and M(4) muscarinic acetylcholine receptors.
Brain Res, 915 (1): 70-8. [PMID:11578621]
5. Hirose H, Aoki I, Kimura T, Fujikawa T, Numazawa T, Sasaki K, Sato A, Hasegawa T, Nishikibe M, Mitsuya M et al.. (2001)
Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity.
J Pharmacol Exp Ther, 297 (2): 790-7. [PMID:11303071]
6. Jakubík J, Bacáková L, el-Fakahany EE, Tucek S. (1995)
Subtype selectivity of the positive allosteric action of alcuronium at cloned M1-M5 muscarinic acetylcholine receptors.
J Pharmacol Exp Ther, 274 (3): 1077-83. [PMID:7562472]
7. Jakubík J, Bacáková L, El-Fakahany EE, Tucek S. (1997)
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
Mol Pharmacol, 52 (1): 172-9. [PMID:9224827]
8. Jakubík J, El-Fakahany EE, Dolezal V. (2006)
Differences in kinetics of xanomeline binding and selectivity of activation of G proteins at M(1) and M(2) muscarinic acetylcholine receptors.
Mol Pharmacol, 70 (2): 656-66. [PMID:16675658]
9. Jolkkonen M, van Giersbergen PL, Hellman U, Wernstedt C, Karlsson E. (1994)
A toxin from the green mamba Dendroaspis angusticeps: amino acid sequence and selectivity for muscarinic m4 receptors.
FEBS Lett, 352 (1): 91-4. [PMID:7925952]
10. Khattar SK, Bora RS, Priyadarsiny P, Gupta D, Khanna A, Narayanan KL, Babu V, Chugh A, Saini KS. (2006)
High level stable expression of pharmacologically active human M1-M5 muscarinic receptor subtypes in mammalian cells.
Biotechnol Lett, 28 (2): 121-9. [PMID:16369696]
11. Lazareno S, Birdsall NJ. (1995)
Detection, quantitation, and verification of allosteric interactions of agents with labeled and unlabeled ligands at G protein-coupled receptors: interactions of strychnine and acetylcholine at muscarinic receptors.
Mol Pharmacol, 48 (2): 362-78. [PMID:7651370]
12. Stein R, Pinkas-Kramarski R, Sokolovsky M. (1988)
Cloned M1 muscarinic receptors mediate both adenylate cyclase inhibition and phosphoinositide turnover.
EMBO J, 7 (10): 3031-5. [PMID:2846274]
13. Vuckovic Z, Gentry PR, Berizzi AE, Hirata K, Varghese S, Thompson G, van der Westhuizen ET, Burger WAC, Rahmani R, Valant C et al.. (2019)
Crystal structure of the M5 muscarinic acetylcholine receptor.
Proc Natl Acad Sci USA, 116 (51): 26001-26007. [PMID:31772027]
14. Wang SZ, el-Fakahany EE. (1993)
Application of transfected cell lines in studies of functional receptor subtype selectivity of muscarinic agonists.
J Pharmacol Exp Ther, 266 (1): 237-43. [PMID:7687290]